Sciencemadness Discussion Board

1-hexene reaction

Gloww - 27-10-2013 at 12:47

Does anyone know how to make 1-hexene into hexane with a deuterium atom at a terminal carbon?

vulture - 27-10-2013 at 12:49

Is this a homework question? The answer is pretty simple and can be found (or deduced) by considering addition reactions to double bonds.

P.S.: We generally appreciate it when you do your homework before asking questions: Search and provide as much details as possible.

Gloww - 27-10-2013 at 13:16

Yes, homework question. I did try to solve it and I coudn't, that's why I went on this website.

Wouldn't D bond to the more substituted carbon though, not the terminal carbon? I can't find any information on that

[Edited on 27-10-2013 by Gloww]

vulture - 27-10-2013 at 14:18

Quote:

I can't find any information on that


http://en.wikipedia.org/wiki/Hydrohalogenation


Gloww - 27-10-2013 at 14:28

Quote: Originally posted by vulture  
Quote:

I can't find any information on that


http://en.wikipedia.org/wiki/Hydrohalogenation



any way you can be more dry and unpleasant??

thanks for the link, unsubscribing from this site

turd - 27-10-2013 at 14:48

Quote:
any way you can be more dry and unpleasant??

You were disingenuous, asked about gratis spoon-feeding and wonder about a less than warm welcome? You may not realize, but vulture is helping you by teaching you how to think like a chemist.

That being said, I'm not sure if the link was the correct one, since the homework is about double-bond reduction to the alkane. The WWW features myriads of overview documents on reduction mechanisms like this one:
http://www.chem.wwu.edu/pavia/chap14c.ppt
The expected answer is in there.

vulture - 27-10-2013 at 16:05

Quote:

any way you can be more dry and unpleasant??

thanks for the link, unsubscribing from this site


Yes.

Don't let the door hit you on the way out.

Turd, I figured to only way to get only a deuterium at the terminal carbon is addition of DBr (or similar), followed by dehalogenation with BuLi and protonation. If there's a better method, please share.

turd - 27-10-2013 at 23:36

Since OP left: Hydroboration followed by deuterolysis?

vulture - 28-10-2013 at 01:41

Wouldn't you get the deutero-alcohol?

turd - 28-10-2013 at 02:41

The alcohol would be obtained by hydroboration/oxidation.

CH3COOD for deuterolysis is actually quite cheap:
http://www.sigmaaldrich.com/catalog/product/aldrich/151777

The expected answer depends of course on the context in which the question was asked. The failure to provide it is more proof that OP is not the smartest tool in the shed. :-/

bfesser - 28-10-2013 at 07:03

Quote: Originally posted by vulture  
Don't let the door hit you on the way out.
I'm so glad you're back, vulture. Now I don't have to make the smart-ass comments like this and get myself into trouble. :P

Gloww, zero-effort posts warrant zero-effort replies.